Speaking of homebrew: As a new homebrew user, I really appreciate Brewfiles, kept in version control with other dotfiles, installed/updated via brew bundle -v
I hope they add support for installing Homebrew itself with Cakebrew soon -- that's the one caveat I see that makes me hesitate to recommend this to newbies. If the goal is to avoid the terminal, having to use the terminal in the installation process isn't great.
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[ 54.7 ms ] story [ 497 ms ] threadThe cake is a lie, though. :)
You can upgrade cask installs via an interactive prompt. You can automate this as well with a login or logout script in your MDM
brew cu -a will look at all your cask installs and let you know what’s out of date, then prompt to upgrade them all, interactive upgrade, or none.
See more info in the semi official docs of the subcommand: https://github.com/Homebrew/homebrew-bundle